English translation:
the more・about
to the extent that
so much… that
Structure
Verb + ほど
Noun + ほど
いAdj + ほど
なAdj + な・ ほど
I had trouble understanding the example sentence
調子がいいほど、慎重に行動すべきだ。
because the ほど is actually the ~ば…~ほど grammar with the ~ば dropped.
I think it would be better to mention the fact that the ~ば can be dropped out on the ~ば…~ほど page, move the sentence above to that page, and remove the “the more” meaning on the ほど page.
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Well now you’ve changed it to 調子がいい時ほど 、慎重に行動すべきだ。and I’m even more confused. Am I the only one who thinks that this sentence doesn’t fit with all the other ones and that " When things are at the extent of progressing well " doesn’t make a lot of sense (I’m not a native English speaker) ?
To me
調子がよければいいほど 、慎重に行動すべきだ。→ The better things are going, the more cautious you should be.
with the よければ dropped would make more sense.
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Hey and welcome on the community forums! 
Yes, you are right this means the same as (the more, the more construction) 
調子が良ければいいほど慎重に注意深くなるべきだ。
Another possible interpretation of this example would be similar to
like ほど は ない construction, but with a positive predicate,、or こそ - emphasizing something, AほどB meaning that B applies to A more than anything. When predicate is positive predicate is usually something like 欲しい、べき, etc.
Examples:
It would be something like this:
試験の前夜ほど、ちゃんと寝ないといけない。(＝試験の前夜ほど、ちゃんと寝ないといけない夜はない）
You must sleep before the night of an exam. You never must sleep as much as at the night before the exam. You must sleep properly especially at the night before the exam.
しんどい時ほど、熱いお茶が欲しいんです。（＝苦しい時ほど、熱いお茶が欲しい時はない）
One wants hot tea when worried. One never wants hot tea as much as when worried. One wants tea especially when worried.
調子がいい時ほど 、慎重に行動すべきだ。（調子がいい時ほど 、慎重に行動すべき時はない）
You should be especially careful when things are progressing good. One never should be as careful as when things are progressing well.
As I said, こそ also would work in those examples. And since we are kinda comparing it with other nights, は also works.
I would say that ば-ほど interpretation fits more, but nevertheless both are possible.
I hope it helps,
Anyway, I will change that example since it is more advanced than it should be
Sorry for the inconvenience 
Cheers!
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Thank you! that makes more sense now.
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Concerning:
今回こんかいは一週間いっしゅうかん ほど 旅行りょこうするつもりだ。
I’m having a hard time finding info from the sources provided about why I should be using ほど instead of くらい/ぐらい. To me, it seems like ほど is more used to express more figurative and hyperbolic statements. This just seems like a realistic statement of “going on a trip for about one week” that would be better filled by くらい/ぐらい.